ChemInform Abstract: Synthesis of New Quinolone Antibiotics Utilizing Azetidine Derivatives Obtained from 1‐Azabicyclo[1.1.0]butane.

Abstract

Ring-opening reactions of azabicyclobutane (II) with thiols or aromatic amines (I) provide access to sulfenylazetidines and aminoazetidines (III). Introducing azetidine derivatives into fluoroquinolonecarboxylic acid (IV) affords the corresponding fluoroquinolone antibiotics. Most of the fluoroquinolones reveal more potent activity profiles vs. Gram-positive bacteria than Gram-negative bacteria. Especially compounds (V) show fairly potent activity against methicillin-resistant S. aureus in comparison with that of levofloxacin. -(IKEE, Y.; HASHIMOTO, K.; KAMINO, M.; NAKASHIMA, M.; HAYASHI, K.; SANO*, S.; SHIRO, M.; NAGAO, Y.; Chem. Pharm. Bull. 56 (2008) 3, 346-356; Grad. Sch. Pharm. Sci., Univ. Tokushima, Sho, Tokushima 770, Japan; Eng.) -H. Hoennerscheid 34-222

Quinolone–Triazole Hybrids and their Biological Activities

“…A series of 3‐sulfenylazetidine quinolone hybrids were assessed for their in vitro antibacterial activities against representative clinically Gram‐positive and Gram‐negative pathogens by Nagao et al . Among them, the 1,2,4‐triazole conjugate 2 (MIC: 0.125–8 μg/mL) exhibited considerable potency in inhibiting the growth of Gram‐positive strains including methicillin‐sensitive S. aureus /MSSA and methicillin‐resistant S. aureus /MRSA, which was as potent as or more active than levofloxacin.…”